(+)-laurene | 18452-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-laurene
• 英文别名: laurene；(+)-Lauren；Lauren；Benzene, 1-[(1R,2S)-1,2-dimethyl-3-methylenecyclopentyl]-4-methyl-；1-[(1R,2S)-1,2-dimethyl-3-methylidenecyclopentyl]-4-methylbenzene
• CAS: 18452-41-0
• 化学式: C₁₅H₂₀
• 分子量: 200.324
• InChiKey: HEVGGTGPGPKZHF-DZGCQCFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902909090

反应信息

• 作为反应物：
  描述：

  (+)-laurene 在 silica gel 作用下， 以 正己烷 为溶剂， 生成 2β,5,5-Trimethyl-2α-p-tolyl-cyclopentanon-(1)
  参考文献：
  名称：

  Laurene，一种来自Laurencia物种的倍半萜碳氢化合物

  摘要：

  Laurene是来自Laurencia glanduliferaKützing和L. nipponica Yamada的一种新的倍半萜碳氢化合物，显示具有结构I。已合成异戊二烯（IV）和Epilaurene（XX）。

  DOI：

  10.1016/s0040-4020(01)82639-9
• 作为产物：
  描述：

  3-甲基-2-环戊烯-1-酮 在 吡啶 、 六甲基磷酰三胺 、 bis(acetylacetonate)nickel(II) 、 lithium aluminium tetrahydride 、 copper(I) bromide dimethylsulfide complex 、 4 A molecular sieve 、 二甲基氯化铝 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 (+)-laurene
  参考文献：
  名称：

  Enantiospecific total synthesis of both enantiomers of laurene by a chemical diastereoselection/lipase-catalyzed kinetic resolution sequence

  摘要：

  A short and efficient enantiospecific total synthesis of natural (+)-laurene and its enantiomer is described. The methodology was developed by employing a stereoselective H-ene reaction of an isocyclic allyltrimethylsilane with paraformaldehyde, followed by a lipase-mediated kinetic resolution of the racemic key intermediate. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00195-0

文献信息

• Total synthesis of (±)-laurene and epilaurene by radical cyclisation reaction
  作者：A. Srikrishna、G. Sunderbabu

  DOI：10.1016/s0040-4039(00)99440-1

  日期：1989.1

  Total synthesis of (±)-laurene and epilaurene, the radical cyclisation of the xanthate () derived from the acetylenic alcohol (), is described.

  描述了（±）-月桂烯和表柔二烯的全合成，即衍生自炔醇（）的黄药（）的自由基环化。
• Ketone methylenation without epimerization: Total synthesis of (±) laurene
  作者：J.E. McMurry、L.A. von Beroldingen

  DOI：10.1016/s0040-4020(01)97334-x

  日期：1974.1

  A total synthesis of the sesquiterpene hydrocarbon laurene, incorporating a non-epimerizing method of ketone methylenation, has been achieved. It is shown that both the phosphonic acid bis(dimethylamide) method of Corey and Kwiatkowski and the phosphite pyrolysis method of Kuwajima are non-epimerizing. For the present case however, the recently published method of Coates [J. Am. Chem. Soc. 94, 4758

  已经实现了倍半萜烃月桂烯的全合成，包括酮甲基化的非表观异构化方法。结果表明，Corey和Kwiatkowski的膦酸双（二甲酰胺）法和Kuwajima的亚磷酸酯热解法均未发生表观不对称。然而，对于目前的情况，最近发表的Coates方法[ J. Am。化学 Soc。94，4758（1972）]是优选的。
• The first enantioselective total synthesis of (+)-laurene
  作者：Hideo Nemoto、Masatoshi Nagamochi、Keiichiro Fukumoto

  DOI：10.1039/c39920001695

  日期：——

  The cyclopentenone 8, synthesised by palladium mediated ring expansion of the chiral vinylcyclobutanols 3 and 4, is converted to the thermodynamically unstable ketone 16 which on methylenation gives (+)-laurene 1.

  通过钯介导手性乙烯基环丁醇 3 和 4 的扩环合成的环戊烯酮 8 被转化为热力学上不稳定的酮 16，经甲基化后得到 (+)- 月桂烯 1。
• Six New Sesquiterpenoids from the Red Alga<i>Laurencia nipponica</i>Yamada
  作者：Teruaki Suzuki、Hajime Kikuchi、Etsuro Kurosawa

  DOI：10.1246/bcsj.55.1561

  日期：1982.5

  Six new laurane-type sesquiterpenoids were isolated from the red alga Laurencia nipponica Yamada and their structures were established on the basis of spectral and chemical evidence.

  从红藻Laurencia nipponica Yamada中分离出六种新的月桂烷型倍半萜类化合物，并根据光谱和化学证据确定了其结构。
• Conformational Control in the Cyclization of an Unsaturated Vinyllithium: Synthesis of (.+-.)-Laurene
  作者：William F. Bailey、Xing-Long Jiang、Carla E. McLeod

  DOI：10.1021/jo00129a020

  日期：1995.12

  The olefinic vinyllithium 2, derived from 2-bromo-5-methyl-5-(4-methylphenyl)-1,6-heptadiene (3) by low-temperature lithium-bromine exchange, undergoes a diastereoselective B-exo cyclization at 0 degrees C in the presence of TMEDA to afford the naturally occurring sesquiterpene (+/-)-laurene (1) in 60% isolated yield along with 17% of the isomeric (+/-)-epilaurene (4). The diastereoselectivity of the cyclization of 2 is discussed in terms of a transition state for the process that approximates a chair cyclohexane which preferentially adopts a conformation having a pseudoaxial p-tolyl moiety and a pseudoequatorial methyl group at the geminally substituted carbon. In contrast to the behavior of 2, radical-mediated cyclization of 3 proceeds entirely in a 6-endo fashion to give 4-methyl-4-(4-methylphenyl)-1-methylenecyclohexan (6) in 93% yield.